4-(4(5)-phenylimidazol-2-yl)pyridine | 59282-87-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4(5)-phenylimidazol-2-yl)pyridine
• 英文别名: 4-phenyl-2-(4-pyridyl)imidazole；4-(4-phenyl-1(3)H-imidazol-2-yl)-pyridine；4-(4-Phenyl-1H-imidazol-2-yl)pyridine；4-(5-phenyl-1H-imidazol-2-yl)pyridine
• CAS: 59282-87-0
• 化学式: C₁₄H₁₁N₃
• 分子量: 221.261
• InChiKey: ALTJKNQLXJJFCN-UHFFFAOYSA-N

物化性质

• 熔点：
  238-240 °C(Solv: ethanol (64-17-5))
• 沸点：
  501.2±33.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯乙酮 在 ammonium acetate 、 氢溴酸 、 二甲基亚砜 作用下， 以 甲醇 、 水 、 二甲基亚砜 为溶剂， 反应 36.0h， 生成 4-(4(5)-phenylimidazol-2-yl)pyridine
  参考文献：
  名称：

  从酮和醛模块合成二取代和三取代的咪唑：激酶抑制剂的途径。

  摘要：

  基于酮氧化，采用催化HBr和DMSO，然后通过咪唑与醛的缩合反应，开发了一种单罐模块化方法，用于合成2,4（5）-二取代的咪唑。该方法提供了二十九个二取代的NH-咪唑（23％-85％的产率）。通过采用这种氧化-缩合方案，然后在咪唑环中进行溴化和Suzuki偶联，得到三取代的NH-咪唑（23％-69％，三步法），实现了三步合成20种激酶抑制剂的过程。该方法还用于合成已知抑制剂GSK3037619A。

  DOI：

  10.1021/acs.joc.9b01844

文献信息

• 2,4(5)-Diarylimidazoles: Synthesis and biological evaluation of a new class of sodium channel blockers against hNav1.2
  作者：Mirko Rivara、Aparna R. Baheti、Marco Fantini、Giuseppe Cocconcelli、Chiara Ghiron、Christopher L. Kalmar、Natasha Singh、Ellen C. Merrick、Manoj K. Patel、Valentina Zuliani

  DOI：10.1016/j.bmcl.2008.09.036

  日期：2008.10

  4(5)-diarylimidazoles were prepared through a simple and efficient synthesis and evaluated as potential inhibitors of hNa(v)1.2 sodium channel currents. One member of this series (4) exhibited profound inhibition of Na(v)1.2 currents, emerging as a promising lead compound for further structure-activity relationship studies for the development of novel sodium channel blockers.

  通过简单有效的合成方法制备了少量的新型2,4（5）-二芳基咪唑，并将其评估为hNa（v）1.2钠通道电流的潜在抑制剂。该系列的一个成员（4）表现出对Na（v）1.2电流的强烈抑制作用，作为一种有前途的先导化合物，可用于进一步的结构-活性关系研究，以开发新型钠通道阻滞剂。
• Structure–activity relationship studies on 2-heteroaryl-4-arylimidazoles NPY5 receptor antagonists
  作者：Richard L. Elliott、Robert M. Oliver、Janet A. LaFlamme、Melissa L. Gillaspy、Marlys Hammond、Richard F. Hank、Tristan S. Maurer、Demetria L. Baker、Paul A. DaSilva-Jardine、Ralph W. Stevenson、Christine M. Mack、James V. Cassella

  DOI：10.1016/s0960-894x(03)00747-9

  日期：2003.10

  A series of 2-heteroaryl-4-arylimidazoles with potent in vitro activity at the NPY5 receptor was developed. Introduction of electron-withdrawing groups on the 4-aryl ring led to a significant improvement of in vitro potency. Several analogues from this series had anorectic activity in rodent feeding models, but were also found to have undesired behavioral effects in spontaneous locomotor activity. (C) 2003 Elsevier Ltd. All rights reserved.
• A facile and eco-friendly synthesis of diarylthiazoles and diarylimidazoles in water
  作者：Dalip Kumar、N. Maruthi Kumar、Gautam Patel、Sudeep Gupta、Rajender S. Varma

  DOI：10.1016/j.tetlet.2011.02.069

  日期：2011.4

  A simple, efficient and high yielding greener protocol for the synthesis of substituted thiazoles and imidazoles is described that utilizes the reaction of readily available alpha-tosyloxy ketones with variety of thioamides/amidines in water. (C) 2011 Elsevier Ltd. All rights reserved.
• Anticonvulsant activity of 2,4(1H)-diarylimidazoles in mice and rats acute seizure models
  作者：Valentina Zuliani、Marco Fantini、Aradhya Nigam、James P. Stables、Manoj K. Patel、Mirko Rivara

  DOI：10.1016/j.bmc.2010.09.029

  日期：2010.11.15

  2,4(1H)-Diarylimidazoles have been previously shown to inhibit hNaV1.2 sodium (Na) channel currents. Since many of the clinically used anticonvulsants are known to inhibit Na channels as an important mechanism of their action, these compounds were tested in two acute rodent seizure models for anticonvulsant activity (MES and scMet) and for sedative and ataxic side effects. Compounds exhibiting antiepileptic activity were further tested to establish a dose response curve (ED(50)). The experimental data identified four compounds with anticonvulsant activity in the MES acute seizure rodent model (compound 10, ED(50) = 61.7 mg/kg; compound 13, ED(50) = 46.8 mg/kg, compound 17, ED(50) = 129.5 mg/kg and compound 20, ED(50) = 136.7 mg/kg). Protective indexes (PI = TD(50)/ED(50)) ranged from 2.1 (compound 10) to greater than 3.6 (compounds 13, 17 and 20). All four compounds were shown to inhibit hNaV1.2 in a dose dependant manner. Even if a correlation between sodium channel inhibition and anticonvulsant activity was unclear, these studies identify four Na channel antagonists with anticonvulsant activity, providing evidence that these derivatives could be potential drug candidates for development as safe, new and effective antiepileptic drugs (AEDs). (C) 2010 Elsevier Ltd. All rights reserved.
• A Practical Synthesis of 2,4(5)-Diarylimidazoles from Simple Building Blocks
  作者：Valentina Zuliani、Giuseppe Cocconcelli、Marco Fantini、Chiara Ghiron、Mirko Rivara

  DOI：10.1021/jo070187d

  日期：2007.6.1

  A simple and efficient approach to selectively obtain 2,4(5)-diarylimidazoles suppressing formation of 2-aroyl-4(5)-arylimidazoles is described. The yield of each of the two products strongly depends on the reaction conditions employed. This reaction provides a simple method to prepare small libraries of biologically active compounds by parallel synthesis.